Three limonoids named thaixylomolins A-C (1-3), featuring two new motifs, were isolated from the seeds of a Thai mangrove, Xylocarpus moluccensis. The absolute configurations of these limonoids were determined by extensive NMR investigations, single-crystal X-ray diffraction analysis, and circular-dichroism spectroscopy in combination with quantum-chemical calculations. Thaixylomolin B exhibited inhibitory activity against nitric oxide production in lipopolysaccharide and IFN-γ-induced RAW264.7 murine macrophages with an IC50 value of 84.3 μM.
SummaryDecandrinin (1), an unprecedented C9-spiro-fused 7,8-seco-ent-abietane, was obtained from the bark of an Indian mangrove, Ceriops decandra, collected in the estuary of Godavari, Andhra Pradesh. The constitution and the relative configuration of 1 were determined by HRMS (ESI) and extensive NMR investigations, and the absolute configuration by circular dichroism (CD) and optical-rotatory dispersion (ORD) spectroscopy in combination with quantum-chemical calculations. Decandrinin is the first 7,8-seco-ent-abietane.
Thaixylomolins A-C: Limonoids Featuring Two New Motifs from the Thai Xylocarpus moluccensis. -Thaixylomolins A (I), B (IIa), and C (IIb) are isolated and their absolute configurations determined. Compound (IIa) exhibits inhibitory activity against nitric oxide production in lipopolysaccharide and IFN-γ-induced RAW264.7 murine macrophages. -(LI, J.; LI, M.-Y.; BRUHN, T.; KATELE, F. Z.; XIAO, Q.; PEDPRADAB, P.; WU*, J.; BRINGMANN, G.; Org. Lett. 15 (2013) 14, 3682-3685, http://dx.doi.org/10.1021/ol401556m ; Coll. Pharm., Jinan Univ., Guangzhou 510632, Peop. Rep. China; Eng.) -Roessler 49-204
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